7,8,9,10-tetrahalo-6h-cyclohepta-(b)-quinolines



United States Patent 3,232,945 7,8,9,IO-TETRAHALO-GH-CYCLOHEPTA- (b)-QUINOLINES Max V. Sigal, Jr., Indianapolis, Ind, and Bernard J. Brent and Paolo Marchini, Bristol, Tenn, assignors to The S. E. Massengill Company, Bristol, Tenn. N0 Drawing. Filed Aug. 13, 1962, Ser. No. 216,342 10 Claims. (Cl. 260-288) The present invention relates to new acridine derivatives, and more particularly to aminoacridine derivatives with an unusually high degree of activity which makes the same suitable for use as antidepressants, and the like.

It is a primary object of the present invention to provide a new series of acridine derivatives.

It is another object of the present invention to provide for methods of producing the new acridine derivatives of the present invention and for methods of using the same as antidepressants.

It is another object of the present invention to provide new 1,2,3,4-tetr-ahydroacridine derivatives which have antidepressant activity and other important properties.

It is yet another object of the present invention to provide new 7,8,9,l0-tetrahydro-6H-cyclohepta-(b)-qinoline derivatives which also have excellent antidepressant activity.

It is a further object of the present invention to provide new acridine derivatives all of which are highly active as central stimulants through central cholinergic and/or monoarninooxidase inhibiting properties, and many of which compounds exhibit analgesic, sedative, and ataractic activity.

Other objects and advantages of the present invention will be apparent from a further reading of the specification and of the appended claims.

With the above and other objects in view, the present invention mainly comprises a compound selected from the group consisting of compounds of the following general formula:

R Y I wherein R is selected from the group consisting of: (1) Chlorine (2) Hydroxy, with the H linked to the N-atorn and R being =0 (3) Amino (4) Substituted phenoxy (5) 3-dimethylaminopropylamine -NHCH CH CH -N- CH 2 (6) (4- (Z-hydroxyethyl) piperazinyl) propyiamino -NH(CH2)a-N NCH2CH2OH N (7) (1-methy1-3-piperidyl) methylamine-NHCH2 (8) 3- (4-earbamoylpiperidine) propylamine O NH (CH2) 3N Fi l-NH:

3,232,945 Patented Feb. 1, 1956 (9) 3-(l-methyl--piperazinyl) propylamine (10) 3-(4- (acotoxyethyl)-piperaziny1) propylamiue (l1) 2- (N -methyl-2-piperidy) ethylamino-N H 0 H2O H (12) 3-dimethylamino-2-methylpropylamino C Ha wherein Y is selected from the group consisting of hydrogen, chlorine, lower alkyl and methoxy; wherein Z to gether with the two carbon atoms to which it is attached is selected from the group consisting of cyclohexane, methyl substituted cyclohexane, trifluoromethyl substituted cyciohexane, methoxysubstituted cyclohexane, methylrnercapto-su-bstituted cyclohexane (Z not being unsubstituted when Y is hydrogen), and cycloheptane; and non-toxic acid addition salts thereof.

When Z is unsubstituted or substituted cyclohexane, then the compounds of the present invention are of the following formula:

wherein R and Y have the same definitions as above and wherein X is selected from the group consisting of hydrogen, methyl, trifluoromethyl, methoxy and methylmercapto.

When Z is cycloheptane then the compounds of the present invention are of the following general formula:

Replacement of the hydroxyl in R position is accomplished in the usual manner with POCI In the case of the cyclohexanone compounds the treatment of the 9-chloro compounds with ammonia in boiling cresol results in the production of the corresponding amines. In certain instances, particularly with the 7-substituted 9-chloroacridines the 9-cresoxy derivatives is first isolated.

In the case of the cycloheptanone compounds treatment of the ll-chloro compounds with ammonia in boiling cresol results in the production of the corresponding amine. In certain cases, particularly with the 2-substituted ll-ehloro compounds, the ll-cresoxy derivative is first isolated.

As indicated above, the compounds of the present invention possess unusual central stimulant activity through central cholinergic or monoamino oxidase inhibiting properties. In addition some of the compounds exhibit analgesic, sedative, ataractic and/ or anticholinergic activity.

The following examples are given to further illustrate the present invention. The scope of the invention is not, however, meant to be limited to the specific details of the examples.

EXAMPLE 1 -meth yl-J ,2,3,4 -tetrahydro-Q-acridine To a mixture of Z-carbethoxycyclohexanone (30 g.) and o-toluidine (19.5 g.), benzene (250 ml.) and cone. HCl (4 drops) was added. The solution was refluxed with a water-separator until the calculated amount of water was collected. The solvent was removed in vacuo leaving a viscous oil (48 g.) which without further purification was added dropwise to stirred mineral oil at 280 C. This temperature was maintained for thirty minutes after addition was complete and, after cooling, the solid was recovered by filtration. The crude S-methyl-1,2,3,4-tetrahydroacridine was crystallized from absolute ethyl alcohol to yield 34 g. (M.P. 334335 C.).

Calc. for C H NO: C, 78.84; H, 7.09. Found: C, 78.09; H, 6.91.

EXAMPLE 2 5 -n 1ethyl-9-chl0r0-1 ,2,3,4-te trahydroacridine 5-methyl-1,2,3,4-tetrahydro 9 acridone g.) was added, with swirling, to POCl ml.) and the mixture refluxed for one hour. After cooling to room temperature the mixture was triturated with crushed ice (400 ml.) and again allowed to come to room temperature. After treating with charcoal and alkalinizing to pH 9.5 with cone. NH OH the precipitated solid was collected on a filter, extracted with acetone (200 ml. x 3), filtered (hot), and upon cooling yellow crystals were obtained. Wt. 16.5 g. (M.P. 46-47 C.).

Calc. for C H CIN; C, 72.56; H, 6.09; Cl, 15.31; N, 6.05. Found: C, 72.36; H, 6.13; Cl, 14.96; N, 6.37.

EXAMPLE 3 7-chl0r0-9-p-cres0xy-1,2,3,4-tetrahydroacridine 7,9-dichloro-1,2,3,4-tetrahydroacridine (5 g.) was dissolved in p-cresol (50 ml.) and anhydrous NH passed through the solution at reflux temperature for four hours. Upon cooling the mixture was diluted with 100 ml. ether and washed With 2% HCl (35 ml. x 3) and the ether-cresol solution concentrated to about 20 ml. leaving a viscous oil which upon the addition of 100 ml. ether produced brown crystals (2 g.). Recrystallization from absolute alcohol gave 1.4 g. of material melting at 143144 C.

Theory: C, 74.18; H, 5.60; Cl, 10.95; H, 4.32. Found: C, 74.26; H, 5.77; Cl, 11.24; N, 4.14.

EXAMPLE 4 v7-chloro-9-amin0-J,2,3,44ctrahya'roctcridine .In another instance, upon the addition of ether, as described above (Ex-ample 3), to the reaction mixture a solid precipitated which was insoluble in the 2% solution. This solid was dissolved in 50% ethanol and made basic with 50% NaOH. An amorphous material was obtained which after crystallization from absolute ethyl alcohol gave the pure 7-chloro-9-amino-1,2,3,4-tetrahydroacridine (2 g.) M.P. 260 C.

Analysis.Calc. for C H ClN C, 67.10; H, 5.63; N, 12.04. Found: C, 67.16; H, 5.33; N, 12.01.

EXAMPLE 5 9-amin0-5-chlor0-1,2,3,4-tetrahydroacridine 7,9-dichloro-l,2,3,4tetrahydroacridine (5 g.) was dissolved in p-cresol (50 ml.) and anhydrous NH passed through the solution at reflux temperature for four hours. After cooling the mixture was diluted with 200 ml. ether and extracted with 2% HCl (50 ml. x 3). The acid extracts were combined and made basic with 50% NaOH giving an amorphous material. Crystallization from absolute ethyl alcohol gave the pure 9-amino-5-ch1oro- 1,2,3,4-tetrahydroacridine (2 g.) M.P. 189 190 C.

Calc. C H ClN C, 67.10; H, 5.63; N, 12.01. Found: C, 67.11; H, 5.24; N, 11.82.

Following the procedures of Examples 15, the follow ing compounds of Examples 6-37 were prepared:

EXAMPLE 6 C H NO 7-methoxy-I,2,3,4-tetrahydroacridone M.P.: 360 Theory: C, 66.81; H, 5.18 Found: C, 65.89; H, 5.22

EXAMPLE 7 C H NO; 2-methyl-J,2,3,4-tetmhydroacridone M.P.: 352-353 Theory: C, 78.84; H, 7.09 Found: C, 77.82; H, 7.23

EXAMPLE 8 C H NO; 5-methy[-1,2,3,4-tetrahydroacriaone M.P.: 334335 Theory: C, 78.84; H, 7.09 Found: C, 78.09; H, 6.91

Theory: C, 78.84; H, 7.09; N, 6.57

Found: C, 79.13; H, 6.88; N, 6.59

EXAMPLE 10 C15H17NOI 5,8-dimethyl-l,2,3,4-tetrahydroacridone M.P.: 242-243 Theory: C, 79.26; H, 7.54; N, 6.16 Found: C, 79.77; H, 7.29; N, 6.06

EXAMPLE 11 C15H17NO; 5-ethyl-1,2,3,4-tetrahydroacridone M.P.: 298-299 Theory: C, 79.26; H, 7.54 Found: C, 79.22; H, 7.48

EXAMPLE 12 C15H17NO; 6,8-dimethyl-1,2,3,4-tetrahydroacridone M.P.: 320322 Theory: C, 79.26; H, 7.54; N, 6.16 Found: C, 79.23; H, 7.16; N, 6.21

EXAMPLE 13 C H CIN; 9-chl0r0-2-methyl-1,2,3,4-tetrahydroacridine M.P.: 6364 Theory: C, 72.56; H, 6.09; Cl, 15.31; N, 6.05 Found: C, 72.75; H, 6.20; Cl, 15.09; N, 6.22

Theory: C, 72.56; H, 6.09; Cl, 15.31; N, 6.05

Found: C, 72.31; H, 5.98; Cl, 15.35; N, 6.12

EXAMPLE 16 C H ClN; 9-chl0r0-5,8-dimethyl-1,2,3,4-teimhydr0- acridine Theory: C, 73.01; H, 6.95; Cl, 14.37

Found: C, 72.76; H, 6.80; Cl, 14.38

EXAMPLE 17 C H ClN; 9-chl0r0-6,8-dimethyl-I,2,3,4-tetrahydr0 acridine M.P.: 89-90 Theory: C, 73.01; H, 6.95; Cl, 14.37; N, 5.68 Found: C, 73.21; H, 6.90; CI, 14.34; N, 5.74

EXAMPLE 18 C H NO 7-methoxy-9-(4'-methyl-phen0xy -],2,3,4- tetrahydroacridine M.P.; 147-149 Theory: C, 78.97; H, 6.63; N, 4.39 Found: C, 78.15; H, 7.08; N, 4.63

EXAMPLE 19 C H ClNO; 7-chloro-9-(4-m=ethyl-phen0xy)-1,2,3,4- tetrahydroacridine M.P.: 143145 Theory: C, 74.18; H, 5.60; Cl, 10.95; N, 4.32 Found: C, 74.26; H, 5.77; Cl, 11.24; N, 4.14

EXAMPLE 20 C H N 9-amin0-2-methyl-1,2,3,4-tetrahydroacridine M.P.: 202205 Theory: C, 79.20; H, 7.60; N, 13.20 Found: C, 79.92; N, 12.86

EXAMPLE 21 C H N 9-amin0-5-methyl-1,2,3,4-tetra'hydroacridine M.P.: 142-144 Theory: C, 79.20; H, 7.60; N, 13.20 Found: C, 78.40; H, 6.73; N, 13.54

EXAMPLE 22 C H N 9-amz'no-7-methyl-1,2,3,4-tetrahydroacridine M.P.: 222-224 Theory: C, 79.20; H, 7.60; N, 13.20 Found: C, 79.28; H, 7.30; N, 13.28

EXAMPLE 23 C H N O; 9-amin0-7-meIh0xy-1,2,3,4-tetrahydroacridine M.P.: 212-213 Theory: C, 73.65; H, 7.07; N, 12.27 Found: C, 74.79; H, 6.78; N, 12.69

EXAMPLE 24 C H N 9-zrmin0-5-et hyl-1,2,3,4-terra7zydroacridine M.P.: 120-122 Theory: C, 79.61; H, 8.01; N, 12.38 Found: C, 79.48; H, 8.08; N, 12.21

6 EXAMPLE 25 C H N O; 9-amin0-5-methoxy-1,2,3,4-tetrahydroacridine Theory: C, 73.65; H, 7.06; N, 12.27

Found: C, 73.93; H, 7.12; N, 12.00

EXAMPLE 26 C H N 9-amino-4-methyl-1,2,3,4-iezrahyaroaicridine M.P.: 142.144 Theory: C, 79.20; H, 7.60; N, 13.20 Found: C, 79.19; H, 7.68; N, 13.54

EXAMPLE 27 C H ClN 9-amin0-6-chlor0-1,2,3,4-tetrahydr0acridine Theory: C, 67.10; H, 5.63; Cl, 15.23; N, 12.04 Found: C, 66.86.; H, 6.31; Cl, 15.96; N, 12.19

EXAMPLE 28 4 methoxy 7,8,9,10 tefrahydro 6H cycl0hepta-(b)- quinaline-JI-one To a mixture of 2-carbe-thoxycycloheptanone (25 g.) and o-anisidine 16.5 g.), benzene ml.) and cone. HCl (4 drops) Was added. The solution was refluxed With a Water separator until the calculated amount of waterwas collected. The solvent was removed in vacuo leaving a Viscous oil (35 g.) which, Without further purification,

was added dropwise to stirred mineral oil at 280 C. The mixture was allowed to cool and the solid recovered by filtration. The crude 4-methoXy-7,8,9,10-tetrahydro-6H- cyclohepta-(b)-quinoline-11-one crystallized from dimethylformamide to yield 9 g. (MP. 282'284 C.).

Calcd. C H NO C, 74.05; H, 7.04; N, 5.76. Found: C, 73.94; H, 7.02; N, 5.96.

EXAMPLE 29 1 1 chloro 4 meihoxy 7,8,9,10 tetrahydr o 6H- cyclohepta-(b)-quin0line 4 methoxy 7,8,9,l0 tetrahydro 6H cyclohepta- (b)-quinoline-1l-one (8 g.) was added, with swirling, to POCl (11 ml.) and refluxed for one hour. After cooling to room temperature the mixture was triturated with crushed ice g.) and again allowed to come to room temperature. After treating with charcoal and alkalinizing to pH 9.5 with cone. NH OH the precipitated solid was collected on a filter, extracted with acetone, filtered (hot), and upon cooling 11-chloro-4-methoxy-7,8,9,10

tetrahydro-6H-cyclohepta-(b)-quinoline was obtained. Crystallization from acetone yielded 6.5 g. (MP. 133 134 C.).

Ca-lc. C H ClNO: C, 68.83; H, 6.16; C1, 13.54. Found: C, 68.21; H, 5.96; Cl, 13.37.

EXAMPLE 3 0 Z-m ethoxy-I 1- (4-methylphenoxy -7,8,9,10-tetrahydro- 6H cycl0hepta- (b) -quz'n0line 1l-chloro-2-methoXy-7,8,9, 10 tetrahydro-6H-cyclohepta-(b) quinoline (5 g.) was dissolved in paresol (50 ml.) and anhydrous N11 passed through the solution at reflux temperature for four hours. Upon cooling the mixture was diluted with 100 ml. ether and washed with 2% HCl (35 ml. X 3) and the ether-cresol solution concen trated to about 20 ml. leaving a viscous oil which upon the addition of 100 ml. ether produced brown crystals (4.3 g.). Crystallization from 80% ethyl alcohol gave the pure Z-methoxy-l1-(4'-methylphenoxy)-7,8,9,10-tetrahydro-6H-cyclohepta (b)-quinoline-hydrochloride (3 g.) M.P. 184 C.

Cale. CZ2H23NO2'I IC1: C, 71.43; H, 6.49; N, 3.79. Found: C, 72.35; H, 6.10; N, 3.43.

EXAMPLE 31 Z-methoxy-I.7-amino-7,8,9,10-tetrahydr-6H-cycl0hepta- (b)-quz'n0line In another instance, upon the addition of ether, as described above (Example 4), to the reaction mixture a solid precipitated which was insoluble in the 2% HCl solution. This solid was dissolved in 50% ethanol and made basic with 50% NaOH. An amorphous material Was obtained which after crystallization from petroleum ether gave the pure 2-methoxy-11-amino-7,8,9,10-tetra-' hydro-6Hcyclohepta-(b)-quinoline (0.7 g.) M.P. 178

Calc. C15H1gN20; C, 74.35; H. 7.49; N, 11.56. Found: C, 73.90; H, 7.29; N, 11.06.

EXAMPLE 32 I I-amin0-2-metl1yl-7,8,9,1 0-tetrahydr0-6H-cyclohepta- (b)-quin0line- 11-chloro-2-n1ethyl-7,8,9,10-tetrahydro 6H cyclohepta-(b)-quinoline g.) was dissolved in p-cresol (50 ml.) and anhydrous NH passed through the solution at reflux temperature for four hours. After cooling the mixture was diluted with 200 ml. ether. A solid precipitated which was insoluble to 2% HCI washings (50 ml. x 3). This solid was collected, dissolved in 50% ethyl alcohol and made basic with 50% NaOH. An amorphous ma terial was obtained which after crystallization from ethyl acetate gave 3 g. of material melting at 209-210 C.

Following the procedures of Examples 28-32, the compounds of the following Examples 33-58 were prepared:

EXAMPLE 33 C H ClNO; 3-clzl0r0-7,8,9,10-retrahydro-6H-cycl0hepta- (b) -quin0line-11-0ne M.P.: 360 Theory: C, 67.88; H, 5.70; Cl, 14.31; N, 5.66 Found: C, 67.81; H, 5.78; Cl, 14.19; N, 5.72

EXAMPLE 34 CIGHIQNO; 1,4-dimethyl-7,8,9,10-tetrahydr0-6H-cycl0- hepm-(b) -quin0line-11-0ne M.P.: 238239 Theory: 0, 79.63; H, 7.93; N, 5.81 Found: C, 76.69; H, 8.08; N, 5.92

EXAMPLE 35 C H NO 4-meth0xy-7,8,9,10-tetrahydr0-6H-cycl0- hepm-(b)-quin0line-11-0ne M.P.: 282-284 Theory: C, 74.05; H, 7.04; N, 76 Found: C, 73.94; H, 7.02; N, 5.96

EXAMPLE 36 C H NO; 4-methyl-7,8,9,10-tetrahydr0-6H-cycloheptw-(b) -quin0line-11-0-ne Theory: C, 79.26; H, 7.54; N, 6.16 Found: C, 79.61; H, 7.35; N, 6.26

EXAMPLE 37 M.P.: 264265 Theory: C, 67.87; H, 5.70; Cl, 14.32 Found: C, 68.06; H, 5.79; CI, 14.63

EXAMPLE 38 C15H17NO2; 2-meth0xy-7,8,9,10-tetrahydr0-6H-cyclohepta-(b)-quin0line-11-0ne M.P.: 360 Theory: C, 74.04; H, 7.04; N, 5.76 Found: C, 73.85; H, 6.98; N. 5.96

8 EXAMPLE 39 C H CINO; 2-chlor0-7,8,9,10-tetrahydr0-6H-cycl0- hepta-(b)-quin0line-1l-0ne M.P.: 360 Theory: C, 67.88; H, 5.70; Cl, 32 Found: C, 67.94; H, 5.85; Cl, 14.16

EXAMPLE 40 C H NO; 2-I7zelhyl-7,8,9,10-tetrahydro-6H-cycl0- hepta(b)-quinoline-1 1 -one P/1.P.Z 360 Theory: C, 79.26; H, 7.54; N, 6.16 Found: C, 79.16; H, 7.17; N, 6.41

EXAMPLE 41 C H ClN; 1 1-chl0r0-4-ethyl-7,8,9,l0-telrahydr0-6H- cyclohepta- (b)-qzzin0line Theory: C, 73.98; H, 6.98; Cl, 13.65 Found: C, 73.69; H, 6.82; Cl, 13.70

EXAMPLE 42 C H ClN; 11-chl0r0-1,4-a'imethyl-7,8,9,10-tetrahydro- 6H-cycl0lzepta-(b)-quin0line M.P.: 88-90 Theory: C, 73.98; H, 6.98; Cl, 13.65 Found: C, 74.31; H, 6.01; Cl, 13.82

EXAMPLE 43 EXAMPLE 44 C H CINO; 11-chl0r0-4-meth0xy-7,8,9,10-tetrahya'ro- 6H-cyclohepta-(b)-quin0line M.P.: 133134 Theory: C, 68.83; H, 6.16; Cl, 13.54 Found: C, 68.21; H, 5.96; Cl, 13.37

EXAMPLE 45 C H ClN; 1Z-chl0r0-4-merind-7,8,9,10-tetrahydr06H- cyclohepta-(b)-quin0line Theory: C, 73.31; H, 6.56; Cl, 14.43 Found: C, 72.59; H, 6.67; Cl, 14.54

EXAMPLE 46 C H Cl N; 2 ,1 J -dichl0r0-7,8,9,1 0-tetrahydr0-6H -cyclohepta-(b) -quinoline Theory: C, 63.16; H, 4.92; Cl, 26.65 Found: C, 62.85; H, 4.84; C], 26.37

EXAMPLE 47 C H ClNO; 11-chl0r0-2-meth0xy-7,8,9,1O-tetrahydro- 6H -cycl0hepta- (b)-quin0line Theory: C, 68.83; H, 6.16; CI, 13.54 Found: C, 69.57; H, 6.11; Cl, 13.08

EXAMPLE 48 C H ClN Z1-chloro-2-methyl-7,8,9,10-Tetrahya'r0-6H- cyclohepta-(b)-quin0line M.P.: 7980 Theory: C, 73.31; H, 6.56; Cl, 14.43; N, 5.70

, Found: C, 72.76; H, 6.77; Cl, 14.40; N. 5.95

9 EXAMPLE 49 C H ClN; 11-chl0r0-7,8,9,1O-tetrahydr0-6H-cycl0hepta- (b )-quinline M.P.: 96-98 Theory: C, 72.56; H, 6.09; Cl, 15.31; N, 6.05 Found: C, 72.84; H, 5.95; Cl, 15.41; N, 5.93

EXAMPLE 50 C H ClNO; 1 I-(p-cresoxy -2-chl0r0-7,8,9,J 0-tetrahydro-fiH-cyclohepta- (b)quin 0line M,P.: 110-112 Theory: C, 74.66; H, 5.97; N, 4.15 Found: C, 75.27; H, 5.93; N, 3.86

EXAMPLE 51 C H NO -HCl; the hydrochloride 0 2-meth0xy-1I-(pcresoxy) 7,8,9,10 tetrahydro 6H cycl0hepta-('b)- quinoline M.P.: 180-184 Theory: C, 71.43; H, 6.49; N, 3.79 Found: C, 72.35; H, 6.10; N, 3.43

EXAMPLE 52 C H N 11amino-7,619,]O-tetrahydro-oH-cyclohepta- (b)-quinoline M.P.: 176-177 Theory: C, 79.20; H, 7.60; N, 13.20 Found: C, 79.10; H, 7.59; N, 13.31

EXAMPLE 53 C H N G; 11 amin0-2-meZhyl-7,8,9,10-Ietrahydro-H- cyclohepfa-(b)-quinoline M.P.: 200-202 Theory: C, 79.60; H, 8.02; N, 12.83 Found: C, 79.18; H, 8.82; N, 12.98

EXAMPLE 54 C H N O; 11-aminO-Z-methoxy-7,8,9,10-tezrahydro-6H- cyclohepta-(b)-quinoline M.P.: 178-179 Theory: C, 74.35; H, 7.49; N, 11.56 Found: C, 73.90; H, 7.29; N, 11.06

EXAMPLE 55 C H N 11-amin0-4-methyl-7,8,9,10-tetrahydr0-6H- cyclohepza-(M-quinoline M.P.: 136-138 Theory: C, 79.59; H, 8.01; N, 12.38 Found: C, 80.18; H, 7.47; N, 12.58

EXAMPLE 6 C H N O; 11-amin0-4-melhoxy-7,8,9,l0-zetrahydro-6H- cyclohepta- (b -quirzo.t'ine M.P.: 150152 Theory: C, 74.35; H, 7.49; N, 11.56 Found: C, 75.19; H, 6.83; N, 11.66

EXAMPLE 57 C H ClN J1-amin0-4-chl0r0-7,8,9,10-telrahydro-6H- cyclohepza-(b -quinoline M.P.: 168-170 Theory: C, 68.15; H, 6.13; C1, 1437 Found: C, 67.67; H, 6.37; Cl, 14.24

EXAMPLE 5 8 C H N 1 1 -amino-4-ethyl-7,8,9,10-tetrahydr0-6H- cyclohepta- (b -quin0lz'ne M.P.: 7880 Theory: C, 79.96; N, 11.66 Found: C, 80.06; H, 8.37; N, 11.85

Without further analysis, the foregoing will so fully R Y I wherein R is selected from the group consisting of hydroXyl, amino, chlorine, =0 and lower alkyl substituted phenoxy, wherein Y is selected from the group consisting of hydrogen, lower alkyl, chloro and methoxy, and wherein Z together with the two carbon atoms to which it is attached is cycloheptane, and non-toxic acid addition salts thereof.

2. A compound of the formula:

N112 Y I wherein Y is methoxy and Y is hydrogen.

3. A compound of the formula:

wherein Y is lower alkyl and Y is hydrogen.

4. A compound of the formula:

wherein Y is chlorine and Y is hydrogen.

5. A compound of the formula:

NH: Y I

wherein Y is chlorine and Y is lower alkyl.

6. A compound of the formula:

reveal the gist of the present invention that others can whereinYis methoxy and Y is hydrogen.

7. A compound of the formula:

wherein Y is lower alkyl and Y is hydrogen.

8. A compound of the formula:

wherein Y is chlorine and Y is hydrogen.

9. A compound of the formula:

wherein Y is chlorine and Y is lower alkyl.

10. A compound selected from the group consisting of -meth0Xy-7,8,9, 1 0-tetrahydro-6I-I-cyclohepta- 6 -quinoline-1 l-one 11-ch1oro-4-rnethoxy-7,8,9,1O-tetrahydro-6H-cyclohepta- (b) -quino1ine;

Z-methoxy-l 1-(4-methy1phenoxy)-7,8,9,10-tetrahydro- H-cyclohepta- (b) -quino1ine;

2-meth0Xy-11-amino-7,8,9,10-tetrahydro-6H-cyclohepta- (b -quino1ine;

1 1-amino-2-methy1-7,8,9,10-tetrahydro-6H-cyclohepta- (b -quinoline;

3 -chloro-7,8,9, 1 O-tetrahydro-6H-cyclohepta- (b) -quinoline-1 l-one;

1,4-dimethy1-7,8,9, -tetrahydro-6H-cyc1ohepta- (b) -quinoline-I l-one;

4-methoXy-7,8,9, 1 0-tetrahydro-6H-cyclohepta- (b -quinoline-1 l-one;

4-methy1-7,8,9,10-tetrahydro-6H-cyc1ohcpta-(b) -quinoline-1 l-one;

4-chloro-7,8,9,10-tetrahydro-6H-cyc1ohepta- (b) -quinoline-1 l-one;

2-methoxy-7,8,9,10-tetrahydro-6H-cyclopheta- (b -quinoline-1 l-one;

2-ch1oro-7,8,9,10-tetrahydro-6H-cyc1ohepta- (b -quinoline-1 l-one;

2-methy1-7,8,9,10-tetrahydro-6I-I-cyc1ohepta-(b)-quino- 1ine-11-one;

1l-chloro-4-ethyl-7,8,9,10-tetrahydro- 6H-cyclohepta- (b) -quinoline;

1 1-ch1oro-1,4-dimethyl-7 ,8,9,10-tetrahydro-6H-cyc1ohepta- (b -quinoline;

4,11-dichlor0-7,8 ,9,10-tetrahydro-6H-tetrahydro-6H-cyclohepta- (b)-quino1ine;

1 1-chloro-4-methoxy-7,8,9,10-tetrahydro-6H-cyclohepta- (b) -quinoline;

11-chloro-4-methy1-7,8,9,10-tetrahydro-6H-cyc1ohepta- (b) -quin01ine;

2,11-dich1oro-7,8,9,10-tetrahydro-6H-tetrahydro-6H-cyclohepta-(b -qninoline;

1 1-chloro-2-methoxy-7,8,9,10-tetrahydro-6H-cyclohepta- (b -quinoline;

1 1-chloro-2-methyl-7,8,9,10-tetrahydro-6H-cyc1ohepta- (b -quino1ine;

1 1-ch1oro-7,8,9,10-tetrahydro-6H-cyclohepta-(b)-quinoline;

1I-(p-cresoxy)-2-chloro-7,8,9,10-tetrahydro-6H-cyclohepta- (b) -quino1ine;

the hydrochloride of Z-methoxy-l l-(p-cresoxy) 7,8,9,10-tetrahydro-6H-cyclohepta- (b -quinoline;

11-amino-7,8,9, 1 O-tetrahydro-6I-I-cyc1ohepta- (b -quinoline;

1 1-amino-2-methy1-7,8,9,1Q-tetrahydro-6H-cyc10hepta- (b -quinoline;

11-amino-2-methoXy-7,8,9,10-tetrahydro-6H-cyc1ohepta- (b -quinoline;

1 1-arnino-4-methy1-7,8,9,10-tetrahydro-6H-cyclohepta- (b -quin0line;

l 1-arnino-4-methoXy-7,8,9,l0-tetrahydro-6H-cyclohepta- (b) -quinoline;

1 1-amino-4-chloro-7,8,9,10-tetrahydro-6H-cyc1ohepta- (b -quinoline; and

1 1-amino-4-ethy1-7,8,9, 1 0-tetrahydro-6H-cyclohepta- (b quinoline.

References Cited by the Examiner UNITED STATES PATENTS 1,867,863 7/1932 Muth 260243 2,653,940 9/1953 Johnson 260288 2,892,753 6/1959 Schmidt et a1. 167-65 3,033,866 5/1962 Saggiomo et al. 260279 3,047,461 7/1962 Hardy et a1. 16765 3,122,553 2/1964 Seneca 260279 OTHER REFERENCES Albert: The Acridines, Arnold, 1951, pp. 1, 111, 115, 172, 173, 208 particularly relied upon.

Desai et 2.1.: J. Indian Chem. Soc., vol. 37, pp. 553-6 (1960).

Ettel et a1.: Chem. Abs., v01. 52, cols. 4642-3 (1958).

Magidson et a1.: Chem. Abstracts, Vol. 31, cols. 5800-1 (1937).

Sargent et a1; J. Org. Chem, vol. 11, pages 359-62 (1946).

Sargent et a1.: J. Org. Chem, v01. 12, pages 567-76 (1947).

Stephens et al.: J. Chem. Soc., 1947, pages 1034-9.

NICHOLAS S. RIZZO, Primary Examiner.

IRVING MARCUS, Examiner.

DON M. KERR, DONALD G. DAUS,

Assistant Examiners. 

1. A COMPOUND SELECTED FROM THE GROUP CONSISTING OF COMPOUNDS OF THE FORMULA:
 2. A COMPOUND OF THE FORMULA: 